


Arcana Pimp

by NidoranDuran



Category: Persona 5
Genre: Anal Fingering, Anal Sex, Blow Jobs, Cheating, Cock Worship, Creampie, Double Penetration, F/M, Hand Jobs, Maids, Oral Sex, Plot What Plot/Porn Without Plot, Prostitution, Vaginal Fingering, Vaginal Sex
Language: English
Status: In-Progress
Published: 2017-08-11
Updated: 2017-08-11
Packaged: 2018-12-14 05:08:30
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 11,169
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11776146
Author URL: https://archiveofourown.org/users/NidoranDuran/pseuds/NidoranDuran
Summary: After Sadayo confesses that she misses her old line of work after all and asks her boyfriend Akira to be her pimp–all to help the Phantom Thieves–Akira finds himself in business. But a pimp needs more than one girl, which is where his secret, sinful dating of ten girls at once goes from a good idea to a great idea. Anonymous commission.





	1. Chapter 1

Sadayo Kawakami no longer worked for the maid service, and no longer played the role of 'Becky', thanks to the help of her loving boyfriend, who changed the hearts of the cruel, greedy couple who had been extorting and guilting money out of her to the tune of forcing her to work that second night job as a maid and a prostitute. And yet still, she felt wrong not wearing the maid outfit as she knelt down between Akira's legs, grasping his cock firmly as she peppered it all over with kisses, staring up at him with a smile broad across his face. "You feel extra hard tonight, master." She closed her eyes and rubbed her cheek along his cock, savouring his warmth and his hardness.

With the beautiful teacher biting her lip and nuzzling against his cock, there was nothing Akira could do but savour the way that she leaned into him, moaning and purring excitedly, adoring his cock every which way and showering him with affection and praise, unconditional in how she lavished him. "Did you miss being my slutty maid?" he asked, leaning back and just enjoying the way she bore down upon him with all her affection. It was a bit surprising that she had insisted on putting the 'Becky' outfit back on, but he wasn't going to complain.

"I did," she whined, a perverted, whimpering confession that she wasn't even remotely able to lie her way through as she stared up at him. "I still love being your girlfriend, but that doesn't mean we can't still play, does it?" She licked her lips, hands reaching up along his thighs to grasp at his cock. She was beyond shame now, beyond care or worry about what she was doing, and how much she lusted after her student. It felt too good for her to deny, strange as it was; Akira had saved her from that fate, but even still she felt like it was a natural part of things now.

Akira gave her a solemn nod, not exactly the most talkative of men, but that suited Sadayo just fine as she caressed his cock a little more, then pulled her hands away entirely, settling them back onto her thighs and leaning her head in. She pushed her tongue right down against the underside of his cock and slowly licked her way up, purring excitedly as she sank slowly into her perverted delight. Kawakami had one very specific favorite activity with any of her former clients and especially now with her boyfriend, and that was cock worship. Deep, sloppy, oral reverence, and the bigger the cock was, the more rewarding and delightful it was to serve.

And what a cock Akira had! The kind of size before her was at once both wildly intimidating, and also so big that it deserved her absolute best; there was no way she could in good conscience not give her absolute all to Akira's amazing cock, and with that in mind she got to work, licking all along his shaft with slow, steady, adoring motions, tongue dragging along every inch of thick, throbbing cock flesh. She kept her hands on his thighs to avoid letting them interfere; Sadayo liked using her mouth as much as she could, liked being sloppy and messy and completely brazen in her cock worship, showing off her sluttier side by not letting the crutch that was her hands do all the work. And the bigger the cock in question was, the more impressive it was that she could handle it all with her mouth.

All along the cock she worked, her tongue making sure not to stop across any inch of the amazing shaft before her as she kept her focus forward and on the task at hand. There was something so sweet about the way she worked, inspiring a lust between her legs that left her very excited, but even as she ached with need, she knew she couldn't pull away from her task; this was about Akira's cock, not about her own appetites. That could come later.

From the perspective of the phantom thief lazily leaning back and savouring the lusty sight before him, this was just perfect. Sadayo was gorgeous, and looked even more so in her slutty maid costume, now a relic of her old days as a health delivery worker, but he hardly minded the reminder; after all, if he had not found out his teacher was a prostitute, he would never have been able to help her, or to end up in a relationship with her. It helped that even if she was a bit older than some of the women in her line of work, she looked absolutely great in her maid costume. "If you still want to play at being my slutty little maid cocksucker, then you're going to have to go a little faster," he teased, if only to try and urge her forward.

"Of course, master," Sadayo whined, having already coated his cock in a thick, healthy coating of spit. She knew what he wanted, and all too happily gave him what he wanted. She took his cock head into her mouth, staring up at him with wide eyes as she pushed down, steady and eager to show her talents off as she began to work further down, taking a couple inches into her mouth to start. Her fingers tightened against his thighs as his formidable cock length reminded her what she was in for; she'd taken it down to the base before, and she knew she could do it, but she wanted the bitter reminder to herself that she wasn't to use her hands. It wasn't what Akira deserved.

Steady she went, head bobbing slowly up and down as 'Becky' began to work along his cock. Akira folded his hands behind his head as he lay back against the pillows, happy to watch her at work. There was something so sweetly sinful about the way that Sadayo went at his cock, shameless and eager to please to a degree that seemed almost too great, like she was leaving herself vulnerable in the process. But even that, Akira didn't completely mind, savouring the certainty of knowing that she was utterly without shame as she worked along his cock, the slow and careful approach to sucking him down proving one of his favorite things about her worship.

It always started out slow, always started out controlled and composed, but it couldn't stay that way for long. Usually, Sadayo could make it down to the back of her throat, but once his cock head began to tease entrance down further, she lost herself a little bit, slipped out of control and out of her mind as she pushed herself down, noisily gagging on the thick, throbbing shaft. She knew it was coming, knew taking it would be trouble, but that never stopped her, never shook her. For a teacher, she seemed to never learn, and carelessly began to work steadily onward, moaning as she began to service Akira's cock with a sense of almost self-destructive excitement.

The build up was fast; it didn't take long at all for her to go from everything composed and careful to a more reckless kind of lust, a passion driven by a need to please. Sadayo could never really shake that urge from her, the desire to make someone happy and to ensure that they enjoyed their sexual experiences. It was what inspired her now to throat Akira's unwieldy, fat dick and care about nothing other than pleasuring him. So she went deeper, choking noisier along his cock as she went, fingers tightening against his lap still, and all she could think about was how much she was pushing herself too far, how she was going too all out and walking a dangerous line. But she couldn't bring herself to care about any of that. Not now. Not when she was having so much fun.

Pleasure reinforced something primal within Sadayo, and as she sucked Akira off, she felt a longing to return to that dimension of their relationship. The way that the exchange of money and the dynamic fell, which had reinforced something twisted and excited within her. She didn't understand it much herself, but as she worked her head up and down along his cock with fast, excited motions, all she could think about was how she felt like something was missing from here, and the twisted little twinge of a solution sent a nervous shudder along her spine.

"Faster," Akira groaned, grabbing her pigtails and pushing her down his cock further. He didn't guide her into a rapid facefuck if only because the thrill of being worshiped by someone so recklessly slobbering all over his cock like she was was pleasure enough; taking control would have stripped from it the enticing element of being able to feel her affection and devotion. But he was drawing closer, as every throb of his cock within her tight throat proved, and all he could think about was that brilliant end. "I'm so close, and I'm going to cum right down your throat, so get your mouth down to the base of my cock like a good maid should."

Sadayo whined as she did as she was told, pressing down that last little bit, her eyes going wide as she choked and shivered, drool leaking from her lips, but she didn't care, especially as Akira found himself dragged over the edge by the rush of sensation surging through him. At the core of her most favorite part of the messy, deep, choking ending of her cock worship was being able to feel Akira's cock spasming and twitching with her throat as he came. Every throb sent another shot of thick spunk splashing down her gullet, making her shiver and twist as she accepted his big load right into her stomach, relishing in the depraved thrill of being so firmly taken, of being conquered and cummed inside of.

She closed her eyes and savoured every drop before pulling back up and gasping for air. "Ah, your cock is still as amazing as always," she moaned, biting her lip and shivering as she tried to collect herself. "May I ride you now, master?"

"Please do," Akira said, reaching up to caress her cheeks and run his fingers along her hair. Kawakami looked more desperate and wound up now, and he was all too happy to invite her into his lap, staring up at her delightedly. He could read something in her expression, something he wasn't entirely sure the nature of yet, but he was intrigued, and it kept him wanting to really push her and see where she went with this.

Sadayo pulled herself up onto her knees over his lap and pulled her dress up, lifting the hem over her pelvis and flaunting the utter absence of panties to cover up her puffy, dripping pussy. She was wet and excited, wound up and ready now for whatever she could get, as she seized Akira's cock and pulled him up to her entrance. A little back and forth of her hips helped Sadayo savour the thrill of what she was about to do, brushing his tip up against her slick entrance as she teased him, staring down at the comparison of his thick cock against her small twat. It was an exciting feeling, and she was all too happy to slam her way down onto his cock, throwing her head back as she yelled out, "Master!" at the feeling of his cock utterly filling her. She could hardly contain herself, shuddering with a twisted excitement as she felt the fullness and the tightness of Akira's cock inside of her.

Hands seized Sadayo's hips and urged her to move. "Fuck," Akira groaned, head pressing back into the pillows, but his eyes remaining firmly on her as he guided her without words to start bouncing. Speaking through physical gestures was much more his speed when it was possible, especially during sex; there was something primal about urging his lover to ride his cock; speaking would have been to beg, but here, he was in control and assertive.

Up and down Sadayo began to rock, her body eagerly lighting up with motion and energy as she started to ride Akira's cock. She clung to him tightly, leaning forward and moaning in excitement as she heaved. "I'd better not find out you didn't do your homework," she teased, and it drew a smirk from her student that was a little frustrating for being impossible to read as a reaction, but she pushed it out of her mind as she kept up the bouncing, working up a nice, quick rhythm, impatient and ready to get going as her pussy ached for attention, needy and driven by all the madness and frustration that she so sorely craved.

Once more riding cock in her old maid outfit, the rush of longing returned to Sadayo, a little more concrete in its form this time, a little better understood, and it made her whine nervously as her spine arched back and she felt herself lit up with a curious, guilty sort of longing. "So good," she moaned, ass jiggling excitedly with each slam down onto his cock. It wasn't as easy a sensation to ignore this time, as she began to feel out exactly what she felt like she was missing and what she 'wanted', a perverse and guilty realization that shuddered its way through her as she kept up the attention atop his lap, the bubbling sensation of guilty delight doing her in with a quickness amid everything happening to her.

She missed her old job, in a twisted and insane kind of way. She couldn't help herself on that front. Akira was a wonderful man, and she was happy to be his girlfriend, especially with how he played along with her indulgent fantasies of submission. But Sadayo had developed a bit of a hunger for her old line of work, a vulgar little streak of excitement that once she was without, she finally realized. And now, riding Akira's cock, she was happy, but she felt like there was something to be gained here, something to be talked out, and she couldn't hide it very well on her face.

"Tell me what's bothering you," Akira said as he squeezed her ass, his hips working upward just the faintest bit to encourage her pace faster, meeting her at uneven points just before she would start her descent, to try and urge her to sync up with him and get faster. He knew exactly how to guide her through whatever he so desired, and he didn't hesitate, but clearly there was more at work here than just Kawakami being horny.

Sadayo whined, head rolling back as she bounced harder on his cock, trying to fuck away the worries atop his big dick and not fret too much about anything, but now that she knew Akira was onto her it was even harder to avoid the thoughts. "Ah, I just ... I'm so happy to be your girlfriend, and I'm glad that you're letting me be your slutty maid again, but I feel like something's..." She trailed off, whining in delight but not coming back onto the train of her thought. But she didn't have to; drifting off said it all, underscored the missing something even as she bounced atop his cock, clearly having the time of her life doing so. The pleasure was not in doubt, and she could tell Akira didn't doubt her actual love for him any more, but a crucial element of this all was still gone.

"It's not the same when I'm not paying you?" Akira asked, giving her ass a succinct slap, making her yelp out in surprise, her cheeks burning as she met his eyes. She looked so gorgeous when she was horny, and right now she was absolutely gone.

"No, not quite. But now that we're together, it feels so even and normal. Even when I dress up and call you master." She'd never talked out her feelings before while riding someone's lap; it was an interesting turn of events, and she was surprised by how easy it was for the two of them to talk it out even in the midst of increasingly rapid, heart pounding sex. "Even though you're so dominant..."

Akira gave her ass another slap, and this time her spine arched back, his hands reaching out to squeeze one of her breasts as his hips worked faster up into her. "Did you have something in mind to fix it?" he asked, even as he dialed up the pressure on Kawakami to the speed that he knew was going to leave her too loud and vocally a wreck to help herself. He kept up the pace, mercilessly fucking her into a heap of moans and need, clinging to him and whining as she tried to form words but failed to miserably.

The frustration hit its peak, but now, it was entirely because of Akira. And Sadayo loved him for it. She couldn't get out any words, and in turn that fed into her sexual fire, into her need, and she went all out on his cock in those final intense moments of need, slamming desperately down against his cock as she threw herself down into orgasm, "Master!" being the only word she could force out as she came so hard, the orgasm tearing up through her body with all the heat and fire she could have ever wanted. A twisting, excited wreck, Sadayo happily felt the reward of her hard work surge through her as her orgasm took control of her and overwhelmed her utterly.

With the greedy, slick inner walls tight around his cock and begging for his cum, Akira slammed upward one last time, sheathing his cock inside of his older lover and using his hands to pull her down by the hips, slamming her onto his cock and holding her in place as he came again. With a harsh grunt, his cock erupted, spewing thick, potent cum deep into her womb and leaving her to whine and blush as she was creampied by one of her students, a sensation too sinful and delightful to ever grow tired of.

Sadayo slumped down against her boyfriend, and whined, "You're so good, Akira," to him. It signaled the end of their little game of playing maid and master, and she happily nuzzled into his neck. "Ah, I always feel so warm inside when you cum in me."

Akira held her close for a moment and pecked her on the cheek. "So, you were saying?" he asked, directing her back to the issue at hand. Now that their lust was gone and in the afterglow their heads were a little clearer, a little less ruled by need, he was eager to find out what was troubling her, and to do something about it.

With a whine, Sadayo closed her eyes. She appreciated the moment's reprieve and the chance to think without her libido in the way, and the fact that even still she felt that rumbling sense within her that this wasn't over yet helped her come to the certainty she needed to come to. "I don't miss having to work myself ragged to bankroll the lifestyle of horrible people who blackmailed and guilted me into that life, but... Maybe I miss the work itself, just a little bit."

"Do you want to go back to the old company?" Akira asked, stroking her hair softly. This wasn't dominant master time, but loving boyfriend time. "I can pay for your service again, if that's what bothers you."

"No, not really." She shook her head and kissed along his neck. "Quite the opposite, actually. I know you were paying me with money you made with the Phantom Thieves, but that was money you could have spent better on something else. No, I was wondering if maybe the next step up from client to boyfriend to something else would be..." She bit her lip, a nervous whine spilling from her lips as she pulled back away from him a bit, staring down at Akira and making sure she had his eyes on hers so that he understood how serious she was as she said, "I want you to be my pimp, kind of."

Akira hadn't known what to expect as an answer, but it sure as fuck wasn't that. His eyes went wide and he stared up in confusion at her. "Your pimp?" he asked incredulously, really not having any idea how to follow this up with any kind of sensible response or sanity. This was far past the time where sanity could really do anything.

"I like the idea of being submissive to you more than I should, and not just in bed. I could moonlight a more casual schedule of doing things, and I can give you a cut of it that you can put toward the Phantom Thieves. You deserve the help, and it's a cause I'd be glad to support with my own body." She felt so free as she spoke, like articulating what she felt was what she had needed all this time. "If you're okay with it, of course. I know you were interested in me while I was doing that line of work before, but if things are different now, then--"

"No, it's not," Akira said, leaning up and pecking her lips. "I still love you, no matter what you do. If you want to go back to it, I support you, and if you want to bring me into the business, then I would be happy to be your pimp."

"I want someone who loves me, and who won't use me. You care about me too much to let anyone misuse me or to push me into anything I'm not comfortable with. I feel safe doing it with you." She kissed Akira back, purring softly as she clung to him. "We can talk out specifics, but for now, why don't we get back to what we were doing?" She brushed her thigh against Akira's still rock hard cock and smiled coyly at him.  
*********************************  
"Thank you so much for calling for me!" Sadayo was on her knees, hair done up in the usual pigtails, maid costume fully primed and cleaned up, and she knelt there on her knees in some cheap love motel room, happily staring up at the salary-man in front of her. "My name is Becky, and I'm so happy that you want to fuck my face so badly."

Sadayo's oral fixation had come in handy in getting her back into the game, as she was able to sell herself solely on her oral talents. The old company she worked for never really cared much about that sort of thing, but Akira was as understanding as could be, and happy to let her focus mostly on oral stuff. Sure, men could fuck and creampie her, but the rate she put on her mouth was enticing while still being a good worth for her work, and she was happy to oblige, relishing in the thing she missed most about being her old job; the never ending rush of cock worship she could indulge in.

Her client wasn't very talkative, but as he pushed his pants down and stepped forward, Sadayo was happy to find he made up for it in size, pushing a big dick into her face for her to serve. "Do it," he said, a plain and direct command that she was all too happy to oblige.

"Of course, master!" She hadn't felt so genuinely peppy in this sort of work for so long, and she wasn't putting on any airs as she pressed happily forward and began to lick all along the cock before her, grabbing hold of it so that she could move it around and get her tongue everywhere. There was so much dick, and when her partner was standing, her hands were necessary sometimes to get her tongue along every inch of cock flesh, a priority that she couldn't shake or deny herself as she got happily to work. 

It was the first cock that wasn't Akira's that she'd licked in some time now, and thankfully it was quite an impressive one. As she steadily painted his shaft in a thick coating of saliva with each successive lick, she felt herself working up a nice, eager level of pure need and electricity, and the fact that she was so easily sinking into this madness left her tingling within, feeling the surge of electric need that she had been looking for this whole time. Hands ran along her cheeks and into her hair, and she savoured it; men who were buying her time always touched her differently, and she felt the guiltless delight shudder through her in the process. Was she dirty for having missed this? Yeah, probably, but she was too gleeful now to deny herself this kind of pleasure.

Once she had covered his cock in spit, she pulled back, gasping in delight. "Just like we talked about?" she asked, staring pleadingly, needily up at him, lips half-lidded and smoldering, mouth opening slowly as she invited him in. There was nothing she wanted more than a good, rough facefucking. The kind she used to be on the receiving end with regularity. It was all she wanted, in fact, and she couldn't contain that fact as she squirmed and wriggled excitedly on her knees. Sadayo wanted it bad, and she wasn't even trying to pretend otherwise.

Without a word, the salary-man grabbed hold of her pigtails and slammed her down onto his cock, thrusting harshly forward and burying his thick shaft all the way down into her throat, making her choke happily as she shut her eyes, feeling the slutty thrill wash over her like she had never felt it before. Now that Sadayo had figured out the terms she wished to go by and what it truly was that she sought, everything was finally turning up well for her, and she couldn't resist the eager urge to throw herself down into the madness, sloppily gagging on the thick cock as he began to thrust into her pretty face, pulling her head along by the pigtails for good measure.

The little twinges of pain that came from it were pure ecstasy, as her head and his hips moved in sloppy tandem, not quite in a proper pace, but that only contributed to the intense sloppiness of what they were doing, the wild and pulsating thrill that came from having her mouth and her throat fucked mercilessly. It was such an insane and wild sensation, rooted in particular in the newness of it. She didn't know what this man's tastes were or what he was going to do to her. It was all a sweet, perverted mystery that she was going to uncover as she went, providing something exhilarating. Familiarity was good, and she adored Akira for how the consistent and regular sex was so blissful, but newness was good for a quick fix, and to get her pussy absolutely dripping.

Whoring herself out for the financial sake of her student boyfriend... These words were so insane that at any point before the past few days, they would have sent her running to another city and starting over under a new name. But now she was eager, happily letting this man fuck her mouth as she looked over at the thick stack of yen he'd put down on the table. This was all so real, and this time she wasn't going to be walking away with too skimpy a bill either; Akira's cut was much less than the agency she used to work for, and she was going to be bringing home more money. More money for herself, too. Not for anybody else.

Maybe there was something to this whole racket after all.

Balls slapped against Sadayo's chin as she brutal pace of her facefucking drove on, the happily choking, sputtering 'maid' having her face thoroughly fucked with all the aggression she craved. Her mouth was ravaged without a care for anything other than the orgasm of the man whose name she didn't even know, and to be once more on the receiving end of that bliss was more than she could bear, rubbing her thighs together as the tension built within her pussy. She could hardly control herself, but she kept her hands under control, bracing them against his thighs as he thrust deep down her throat. Putting them between her legs would have done her little good, and the last she wanted was to seem like she was more concerned with her own release.

With drool trickling down her chin and all the sloppy, frustrated noises ringing from her lips, Sadayo was in the blissful peak she craved. Her throat spasmed around the cock shunting its way down her gullet, and the way that she stared up at him grew almost delirious. She wasn't having a great time with breath, but that didn't really bother her at all. How could it? She felt so delighted and lit up with so much bliss that it only served to push her pleasure further in the right direction, to make her twist and writhe excitedly against her own decadent needs. This was a strange kind of ecstasy, but with the steady, unrelenting use of her mouth and the pleasure surging up so hotly within her, it didn't matter; Sadayo needed him to cum, and needed it to be big.

And big it was. The salary-man had been silent throughout save for the occasional grunt and heavy breath, and his orgasm was no different. Sadayo received no warning of what was coming, no word or sign. He just cursed as he came, as he thrust his cock down her throat and his cock erupted, spasming and twitching as it unloaded right down her gullet. But that wasn't enough for him as he started to pull back out again, the cum still gushing out in spurts as it splashed against the back of her throat, down onto her tongue, and with her mouth suddenly full of sperm, finished with a single streak across her face, from her drool-soaked lips up along her cheek.

Sadayo didn't even hesitate to swallow it all down, gulping and whining as her body bucked, a deep shiver running powerfully through her as she stared up at him. The salty taste lingered on her taste buds, and thick, gooey strands of spit hung from her chin as she gasped for air. "Wow! Y-you came so much, master. I'm really glad you had so much fun with me. It was amazing to feel." She bit her lip nervously. He'd paid for a blowjob and nothing else, but Sadayo was hopeful she could work a good hustle and convince him to go again. "Did you have fun fucking Becky's face?"

Staring down at the cum and spit leaking down her chin, the man who'd just left the teacher an absolute wreck could feel his cock remaining rock hard at the sight of her. The way her breath made her chest rise and fall, the way her cheeks were flush and her eyes a little bit bugged out. "Clean your face off," he said, reaching into his wallet and quickly pulling out another bunch of yen. "And then get onto the bed." He put the bills onto the table and looked over to her eagerly.

Sadayo let out a delighted whine. "It's an extra three thousand yen if you want to creampie me!" As she got onto the bed she heard more money slamming down against the table, and could not have been happier to tug up the hem of her dress as she lay on the bed and whined, "Come fill my pussy, master!"  
*******************************  
When the salary-man finally left, Akira slipped back into the room. They'd only booked one appointment as a trial run, but it had gone longer than expected, and when he came by, he saw why; his beloved teacher had been made an absolute mess of. She lay on the bed almost with hearts in her eyes, several loads of cum leaking from her thoroughly fucked pussy and another all over her face. She lay there absolutely breathless, and on the table sat a hefty amount of yen, the cost of the six rounds he'd spent fucking her mouth and her pussy.

"Did you enjoy yourself?" Akira asked, grabbing the money and counting it out quickly. It was all there, thankfully; if it wasn't, he'd have to be paying some visits, but he was glad to see it wouldn't be an issue. He broke it off into two piles, Sadayo's being larger than his own as he slipped his cut into his wallet and walked over to Sadayo. "It looks like you did."

"It was so good," Sadayo whined, lying breathlessly there, staring up at Akira. She was so happy to see him again after the exhilarating sexual thrill ride she'd just been on. "I loved this rest run, and I think I'm ready to go all in on this. Do you still want to be my pimp, Akira?"

"I do," he said happily, leaning forward and smirking. "And I'll make sure you're taken care of. I'd kiss you right now, but you're kind of..."

'Yeah, it's okay." She nodded, rising up from the bed. "I'll go wash up and use some mouthwash, and maybe then we can finish up our time with the room?"

"I'd love that." Akira gave a playful swat to her ass as she walked off. As he sat there, he couldn't help but wonder, given what Sadayo had made in such a short time, whether or not there was some good money in being a pimp. Not that he really had a great enterprise to start with; he would have needed more girls, and more--

Wait a second. It all clicked for Akira in that moment, as he looked down at his phone, and the flurry of hearts he'd had in his unread messages. To some meaning of the word, Akira was already a pimp, given the fact that he was running secret relationships with ten girls all at once. Each of them young, attractive, wonderful girls who would have fetched a pretty dollar. Why was he not turning them out right now? For 'the good of the Phantom Thieves'? It was a question that he really didn't know how to answer now, as he looked up Sadayo in the small bathroom off to the side, washing her face off. None of the girls knew about each other in that way, but maybe once he had them all selling their bodies and bankrolling their crime fighting venture, it would be an easier reveal.

He looked back at his phone, messaged the last girl to send him a message, and not even paying attention to who it was, asked if she'd be free tomorrow to talk.

It was time to go into business.


	2. Hifumi - Twice the Penetration, Twice the Fun

Akira didn't know how to dance around asking Hifumi to become a prostitute. There really wasn't any kind of sane way to do that sort of thing as they sat on the edge of his cot in Cafe Leblanc's attic. There was no delicate way to phrase it, no way to make it sound like anything 'softer' than what it really was, and Akira tried, but as he spoke he felt a simmering nervousness within him as he talked about how it was "for the good of the work he did" and how people did things for those they loved. "So, this is kind of insane to ask my girlfriend, but... Could I become your pimp?"

Through it all, Hifumi sat and she listened, nodding steadily as Akira tried to pitch prostitution to her, and she seemed almost too reasonable in how she let him speak,. how she sat perched in place and let him spin his thread. His insane, insane thread, until he was finally done and she said very matter-of-factly, "I would not mind doing that." She put his affections to rest, leaning in close and kissing Akira on the cheek. "For the good of the Phantom Thieves, and because I love you. Actually, in truth, I... I do have a bit of an interest that may be helpful to this."

Akira perked an eyebrow. "I'm happy to hear that and I love you to, but what is it?" he asked, holding her in close, avoiding the urge to convey the genuine surprise that came with hearing Hifumi so happy to 'work' for him. He had many more girlfriends to get through and wasn't sure how well it would go with the others, but he knew better than to think this was a good pattern, especially when one of them already worked such a job to begin with.

“I have an interest in threesomes,” Hifumi admitted. “Any combination, really. A man and a woman, two men, two women...” She bit her lip, leaning in close to Akira and sighing. “I have a bit of a fascination with threesome porn. I always have, and if we're going to be 'working together' like this, would it be possible to find ways to suit my work more toward those sorts of things? I don't know much about prostitution or if it's possible, but that would make me happiest.” Everything was so plain in how she spoke, which threw Akira for a loop; he felt like they were casually discussing shogi strategy instead of negotiating Hifumi being a whore.

“I think we can do something like that,” Akira said, nodding slowly as he leaned and kissed her again. “I want you to enjoy yourself in what you're doing, after all, so sure, let's do it.” A maid and a lover of threesomes; Akira wondered if he was going to have to suit his business around gimmicks and kinks for each girl, his mind on what his other girlfriends were into and how they would likely have similar demand. This was going to be a mess.

Hifumi smiled, leaning in close and kissing Akira flat on the lips this time. “I'm so glad to hear that. I love you, and I'm sure I'm going to love my side job too. It will be fun to have something without any pressure.”

Akira snaked his hands up along his girlfriend's thighs, pushing her dress up as a wry smile came across his face. Seeing that Hifumi wasn't put off by his offer, he felt like he could now go in with his own touch and have some fun with her. “So, threesomes,” he said, fingers squeezing against her thighs. “What sorts of stuff have you gotten off to? You can tell me, it's okay; I am your boyfriend after all.” He was also the boyfriend of a bunch of other women too, but Hifumi didn't need to know about that yet. “And maybe if there's something we could try together some time...”

Feeling hands at her thighs, Hifumi purred, pressing eagerly against her boyfriend from the side, leaning against his shoulder as she felt the hot touch upon her. “Mm, well, there are a lot of things I like. I try to watch all various combinations of genders, it's all the same to me, as long as I'm able to see multiple people together at once. It's the combinations that really turn me on. But for things to try, I--I've always been curious about eating cum out of another girl's pussy. And um... Nngh, it's a bit embarrassing to admit, but. Double penetration sounds really hot to me.”

Akira's eyes went wide with wicked delight as his hands crept further up her legs and started to tug at her panties. “Oh? Have you fantasized about it before? About being fucked in your ass and your pussy at the same time?” This was all music to his ears, and now Akira couldn't help himself; he wanted to be aggressive, wanted to tease, wanted to prime Hifumi for what she would be doing and to enjoy some of the fun himself. His cock was rock hard at mention of Hifumi fantasizing about eating out a creampied pussy, and he made a mental note of definitely introducing her to one of his other girlfriends at some point--when he had found a way to announce he was dating ten women without it sounding insane--so they could try it out. But wanting to avoid that talk for now and knowing that Hifumi would be much more likely to deal with two men, he wanted to lean more on the opposite to avoid showing his excitement too much while also prepping her fro what was to come.

“A lot,” Hifumi confessed, biting her lip as she felt his hands at her, as he pulled her panties down, her hips rising up off of the bed so he could get them off. “It's what sounds like it would be the most fun, and what I've practiced the most, at--I mean, the...”Hifumi's cheeks lit up as she realized she'd tipped her hand a bit too much there, but Akira was already smiling and leaning in close, his broad grin leaving her knowing she was in for something now.

“It's not embarrassing to practice when you're alone,” Akira said, brushing it off as she guided her down onto her back on the bed, pulling up the hem of her dress to expose her damp pussy as he brought a hand down onto her mound, rubbing it eagerly while he reached the other up to her mouth. “Suck on them,” he said, tapping some fingers against her lips, her mouth happily opening to accept them. He pushed them in, and Hifumi happily began to suck on the pumping digits, moaning as he rocked them steadily in and out of her mouth, getting them nice and slick with her saliva. It left no mystery about where they were going, but that only got Hifumi even hotter. When finally his fingers were nice and slick, he pulled them out and asked with a big, smug grin, “So, which hole do you imagine me taking?”

Hifumi whimpered as she watched the fingers trail down just above her body, remaining slick and wet as he brought them between her legs and then reached down, a single digit trailing back up the cleft of her ass, making her wriggle in excitement. “My ass!” she cried out, biting her lip as she felt the pressure build. 'I like to imagine that I'm riding the lap of another man while you're fucking my ass from behind; that I know you're there, but I'm able to experience the thrill of someone else in the room, able to lock eyes with them and be intimate with someone else for a night. That's not wrong, is it? I hope that doesn't upset you.”

“If it upset me, we wouldn't be going 'into business',” Akira said, justifying it easily enough without dipping into his nine other girlfriends. It was all he needed to hear, and he was happy to go in now for the kill, fingers pushing into his girlfriend's hole at once, claiming her ass and her pussy while his eyes fell eagerly upon Hifumi's face to read her reaction.

“Ah! Yes, Akira, yes!” was all she could say as her face lit up with glee, two fingers each sinking into her holes in tandem, giving her exactly what she had been craving. It was an incredible feeling underscored by the rumbling need within her, by the feeling of ecstasy that naturally followed being able to experience the rawness of being fingered in both holes. They weren't cocks, sure, but it was still something, still the filling of her pussy and her ass at the same time by someone else. “I've only ever used my own fingers and some toys before, b-but you're... Nngh, your fingers feel so much better!” The touch of another was big for Hifumi, which was why she loved the idea of feeling two peoples' touch at the same time. She wouldn't have that here, but it was still more than enough for her to shiver in ecstasy and whine as the pressure swelled up inside of her, an immediate and fervid pulse of excitement giving her precisely what she craved.

Akira shifted his position a a little bit, getting between her legs so he could more easily work at her holes and see what he was doing, her hips rising up off of the bed to give him better access to her ass. He knelt there in prime position to watch her twist for him, to see her beautiful face ignite with all the shameless excitement of a woman getting the decadent treatment she craved so utterly, even if t was embarrassing to admit. “I want to make sure you're ready,” he explained, smiling wide as he worked his fingers into both of Hifumi's holes at once. “Because there will be real cocks going into you at once.”

“I know, I can't wait!” Hifumi bit her lip, head pressing back against the pillow. She felt the fingers working in eager unison at her holes, something that she had always had a bit of a clumsy time trying to do when reaching behind herself to get at her ass. There was no easy or comfortable way to give herself a double stuffing with toys, but Akira's strong, deft fingers were able to give her what she craved without any trouble, and the sensation of being touched like this had her bucking hotly on the bed, losing herself to the raw swell of need and uncontrolled lust that she couldn't believe she was really giving herself to. “I'm going to be fucked by two men at once, and even paid to do it. It's shameful to be this excited, but I can't care, I want it now, Akira!”

This was almost frighteningly easy, and Akira had no idea how he was making this all work out so quickly or how Hifumi was left a gasping, writhing mess happily getting fingerfucked in both holes while happily looking forward to being prostituted. This shouldn't have been so easy, shouldn't have been so smooth, but he wasn't going to complain about the way that this went as he at least had the chance to go all out on Hifumi and ravage her with his fingers hammering eagerly into her. All the moans and writhing and bucking of the needy shogi pro in his bed had Akira's cock raging, but he kept it his needs at bay, ignored what was going through him as he focused harder on what he was doing and the desperation that burned so hotly through Hifumi. It was so hot to watch, and he could feel the pressure heating up within him as he kept his hands moving.

A third finger slipped into each hole as Akira grew bolder, and Hifumi grew even louder in turn, writhing on the bed harder and hotter than she could handle, everything about the raw excitement that shuddered through her proving too good to resist. She was losing control, moaning louder as her legs writhed about wildly. “Faster,” she begged, biting her lip hard, refusing to slow down amid the swell of sensation that bubbled up hotter inside of her. “Oh, Akira, I'm getting close! Please keep going, this is amazing!”

Making it all even better was the fact that soon, it wouldn't be fingers inside of her, but cocks. Real, hard, throbbing dicks hammering into her too fast to process, until her thoughts spun out of control. Not to say that Akira wasn't blowing her mind here, as she writhed on the bed, a howling, blissed out mess begging for more, her face twisting with all manner of lurid, delighted expressions that showed off just how needy she was. Hifumi was a mess and she could not have been happier about it. When finally her orgasm came, her eyes shut tight, face lit up with a wide smile and her mouth open to let out all the needy cries she had built up within her, shoulders lifting off of the bed as she lost herself.

Akira's fingers kept pumping, lovingly fingerfucking her through her orgasm as he gave both holes the love they needed, driven by a desire to lavish Hifumi with the most thorough double fingering experience he could to the ravenous delight of his beautiful shogi pro girlfriend. She looked so happy, so at peace, so ready to surrender completely, and he knew then that she was going to love what she was getting into. "Enjoy yourself?" he asked, withdrawing his fingers slowly from her holes at once, delighting in the way she whined and groaned at the sudden emptiness upon her.

"So much. But... Nngh, I think I'm going to enjoy it so much more when we get to work. I can't wait. When can we start, Akira?":  
******************************  
“I can't believe we're about to have sex with the Venus of Shogi!” shouted one of the men, eagerly undoing his pants, while Hifumi sat nervously on the edge of the bed in some seedy love hotel, forcing a smile as she looked at the two men who had come to visit her. It was her first time, and Akira hadn't had to look hard to find some men who were happy to pay good money to fuck Hifumi Togo, her shogi notoriety immediately attracting the attention of some men who had no aspirations of professional play but who couldn't pass up the opportunity to sleep with a real star. It was an extra little edge of 'realness' to it that had Hifumi not quite second-guessing what she was doing, but certainly feeling a bit more pressure upon her now than before. She was hoping for strangers, hoping for men who would do what they wanted to do with no strings or recognition attached.

But she couldn't let that stop her as she got up off of the bed, forcing her smile wider as she drew closer toward them, sinking slowly down to her knees in front of them and smiling up at them brightly. “I might be the Venus of Shogi, but tonight, I'm yours, and I don't want you to think of me as anything else.” Biting her lip, she went through a revised version of the line she'd been thinking up, nervously concocting things to say so that she wouldn't have to think about them on fly when she was in the thick of it. It was all she could do to help ease her nerves as she watched them get their pants down and their cocks out, eyes going wide as she wrapped her hands around a pair of big, hard dicks that had her smiling excitedly, her demeanor immediately brightening up as she laid her eyes on what she was dealing with. She was used to big dicks thanks to Akira, but never two, and to see what she was dealing with had her chest tightening and her heart pounding; this would be the crazy first threesome she'd been waiting for.

Leaning to the right, Hifumi began to lick along the cock while her hands both worked back and forth with a slow, patient motion, her eyes looking upward at the two men before her. She could feel the pressure on her now, and that a good thing; nervousness did Hifumi no good, but she thrived in high pressure situations. Two men who had paid for her 'company' and expected a good time was precisely the kind of pressure that Hifumi needed. Pressure was a distraction, a way to be pushed into action and to not spend too much time fretting over what she was doing; a tactician should always be careful not to get too hasty in a situation just because pressure was upon them, but spending her life having to make careful, methodical movements on the game board meant that in life, Hifumi appreciated living in the moment a little more.

And what a moment it was. Hands stroked back and forth steadily across the two cocks, while she knelt there wearing absolutely nothing, biting her lip and feeling the pressure build. “Such big cocks,” she purred, trying to give them what she figured they wanted to hear as she shifted over to start licking the other cock as well, wanting to give them both equal attention as she felt her way through this. Hifumi was fine at blowjobs, she'd just never had to give two at once, and she didn't want to get too carried away in what she was doing before she had a solid grasp on the situation and not just on the cocks in question. “Mm, I can't wait to feel them both inside of me.” She laid some kisses onto the head of the left cock before switching back over to the right.

This time, she took the dick into her mouth, moans rumbling hotly as she sucked him down, starting to feel herself quickly sinking into a groove. She'd seen this sort of thing many times before in porn, and was simply going through the motions of repeating what she had watched, what she would get off to at night with a toy buried between her legs. But now it was all real, all right there before her, and she was excited to see where this could go, moaning as she sucked the cock down into her mouth and got to work. Closing her eyes, she didn't try to thin k about the idea that this was normal or just like when she was at home, didn't pretend this was Akira and there was only one man here. No, she wanted to relish in the madness of being very much in the thick of it with two men paying to share her body, refusing to shy away from the reality of the situation.

After a nice, steady sucking, Hifumi swapped over, giving the other cock much the same while her hand slid along the first cock, broadening her strokes so she could rub that saliva in, getting the cock slicker and easier to work over. She could feel the pressure building hotly within herself, feel the aches and need that ignited her into the swell of heat and madness that she had craved so utterly. Hifumi was finally with two men at once, and as she got into the groove of sucking two cocks at once she felt herself ignite with the raw push of excitement she needed. It was real. All of it, all so very real, burning her up as she whined and pushed herself forward, slurping the cock down greedily and letting herself get carried away. When she switched over, she sucked the cock down even deeper, letting him push into the back of her throat as her hands jerked quicker, finding a steadily accelerating pace as everything Hifumi did helped to get her even more worked up about the fact that she was really doing it. This was all actually happening.

Another switch over, and this time she throated the cock, moaning louder and hotter as she slurped and slobbered all over the big dick, her hands working even faster still, drawing excited groans from the men she was fellating, one of them even remarking, “Ah, the Venus of Shogi is a slutty cocksucking pro.” It was a comment that should not have ignited excitement within Hifumi like it did, but she couldn't help but find herself wound up by the promise of how twisted this was, by the opportunity to embrace something raw and vulgar amid the pulsating thrill of what she was doing. They spoke about her so cruelly, but somehow that cruelty only got her even hornier, made her burn with a throbbing excitement that she could get behind. Hifumi wanted more of it, sucking it down deeper even as she gagged loudly, just so she could hear more remarks like that and feel the twisted, depraved glee of knowing they thought so lowly of her.

“Such a lewd mouth from a smart woman. She's the perfect mix of brilliance and sluttiness.” His hand grabbed the back of her head, and as Hifumi swapped over, he pulled her down deep, forcing himself further down her throat, and Hifumi was happy to oblige, moaning loudly amid the sloppy noises of struggle her throat made in the process. It was so raw, and their treatment of her was only making her burn up hotter, making her ache with guiltless delights she could hardly believe she was embracing like she was. Hifumi couldn't get over it, moaning as she swapped back, fingers from the other man's hand entangling into her hair too now as she was guided back and forth by two men both eager to use her as thoroughly as they could. There was something exciting about the two grips on her head, the way they both greedily ached for their own needs to be tended to even though they were supposed to share her. As the men got hotter and tighter wound, Hifumi could really start to feel the need, the ache, the want for her to focus more on them. It excited her, left her moaning around the thick cocks she slurped down without hesitation. There was so much going on and it all fed so sweetly into more than Hifumi could have ever asked for.

The first man came without warning, gasping as his hand tightened on the back of her head, pulling her down onto his cock so he could cum right in her mouth. Hifumi's eyes went wide as the thick, salty goo filled up her mouth, left her moaning excitedly as she took it all, jerking the other cock off faster as he pushed forward forward and prodded her cheek with his cock head, Hifumi surprised when he too came, right there on the side of her face. She figured he would have wanted to cum in her mouth and she could let him add to the gooey mixture she was left with, but instead he gave her a messy side facial. But that was hardly disappointing for the shogi pro, who shivered as she felt the hot spunk trickle down her cheek.

Pulling back, Hifumi happily swallowed the loads down, moaning as she opened her mouth to show off that she had indeed gotten down every drop. “I've never had two cocks before, but yours look so perfect to fuck two of my holes at once. Mm, did I do a good job at sucking your cocks at once?”

“You were amazing, especially if it was your first time.”

“I'm humbled by your shogi prowess and your cocksucking abilities, Togo-sensei.”

“Mm, please, don't be so modest and polite,” she whined, hands rubbing along the slick and spent cocks, which still remained hard and ready for more. “Not here. I'm a whore tonight, so don't worry about my skill at the game, and use me like you would any other woman you would pay for.” She smiled brightly up at them, able to feel the excitement coursing through her. Hifumi was ready now to get what she wanted, loving the chance to suck two cocks, but wanting something else even more now. "Can I please feel your big, amazing cocks double penetrating me?"

She didn't even receive a verbal response as the men grabbed hold of her and dragged her onto the bed, one of them lying on it as the other guided her to climb onto his lap, the eager shogi pro ready for all of it as she moaned, shifting into position and slamming herself down onto his cock with a needy gasp. From behind, the other man leaned in and guided his cock up to her ass, and she was happy to whine as he said, "I'm going to fuck the Venus of Shogi's ass! You're a pricey whore but this is so worth it!" Hifumi was pretty sure he said something else too, but as the cock sank into her ass with her pussy already stuffed with dick she was too busy howling in bliss to hear it, head thrown back as the cocks filled her up more than she could bear.

Bouncing eagerly between their bodies, Hifumi got things rolling, gripping the shirt of the men she rode tightly as she started to rock her hips back and forth, encouraging them to fuck her as she started up her steady, frustrated swell of need. "Fuck me hard," she pleaded. "Pound me with your big cocks at once, let me feel the love of two men using my body at the same time!" This was the dream, something she had never imagined she would actually be doing, and she was so busy having her fantasies come true that she didn't even mind that it involved selling her body like she was. It felt so good that she just let it all happen, let the bliss wash hotly over her as she pushed down onto the cock that sank deep into her pussy, only to slam back against the dick stretching out her ass.

The tightness of the girl's holes both stretched out as they were had the men who were fucking her groaning in excitement, able to feel the other cock moving around inside of her through what felt like a very thinly squeezed wall, but at the same time her body offered up no resistance or fight, nothing to impede their eager thrusting as they gave it to her as hard as she begged for it, the two men winding up to start eagerly hammering away at her perky butt and her slick twat, wanting to get their money's worth for the time they had gotten her for. Back and forth they thrust, cocks hammering forward, sloppy and very out of sync, but it didn't matter to Hifumi, especially because sometimes she'd have that perfect moment where they thrust into her at the same time and she felt so full her cries of pleasure rang through the floor of the love motel, an obnoxious and carelessly driven burst of excitement Hifumi didn't feel the least bit sorry for.

It was just as good as Hifumi could have ever hoped it was, her breath racing as she bucked needily back and forth between them. All those nights spent imagining this very thing happening hadn't prepared her for the rawness of being double stuffed, of two warm bodies pressing against her as two men fucked her at the same time, their touch and their moans mixing together, getting lost in the heated swell of her mind's inability to keep anything straight anymore. All Hifumi wanted was to race toward the brilliant, burning end she knew awaited her, and she could not be stopped now. "I want you to cum inside of me at the same time," she whined. "I want to feel it all. Please, please!" She pleaded with cum still lingering on the left side of her face, leaving a perverted and lurid sight that had her looked even more perverted, as if she needed any help with the lewd expression of pure bliss breaking across her face as the pleasure hit its peak. 

Amid all of Hifumi's moans and howls was the sound of flesh slapping against flesh, bodies colliding noisily as Hifumi endured the rough fucking of two men both eagerly seeking pleasure from her body, thrusting almost carelessly away at her. It was selfish and greedy, lacking in a certain intimacy and intensity that Hifumi usually craved from some of her more tender threesome favorites, but she couldn't even be mad, too busy having the time of her life getting fucked in two holes to worry about how it lacked a certain tenderness. The only things that needed to be tender were her holes after a long day of getting double penetrated for money, and she could instead let Akira bring the love and affection, maybe even with one of his cute friends, if they were interested. Shujin Academy's student body president seemed to hang around her boyfriend a lot and she was an absolute stunner, so maybe she would be a better fit.

It all came to a head, with Hifumi cumming first, because of course she did; being double stuffed with big dicks was bound to get her off faster than she could bear. "Fill me fill me fill me fill me!" she squealed, speaking fast and high as she felt herself overwhelmed, driven over the edge and so happy to feel it. She couldn't have been more elated to feel the big cocks erupt inside of her, as the men slammed forward and grunted, burying their cocks inside of her and letting loose their pent up loads. Hot, thick, gooey seed filled her ass and her pussy at the same time, and everything just felt right, the spunk giving her all the warmth and thrills she could have ever wanted. The throbbing, the pulsating, the fullness... It all drove Hifumi up the wall, and rather than feel herself tire out, she could feel herself ready for more, throwing her head back and gasping in ecstasy.

"That's the two rounds you paid for," she purred, hips wiggling. "But maybe you'd like to extend?"  
*******************************  
When Akira came to check in on Hifumi after a few hours of work, he found her lying on her back atop a table, legs up high in the air as one man hammered away at her pussy, her head leaning off the edge of the table and leaving a clear line from her lips to her throat for the man facefucking her eagerly. She was going through men like a pro, and he was impressed by her speed; she was almost as efficient as Sadayo, but getting off twice as many men at once. He didn't say anything, just standing outside of the room and watching, happy to see her at work. Hifumi had no idea, but two rooms over, Sadayo was worshiping the cock of another pro shogi player, his other turned out girlfriend happily at work for him too. This gambit was definitely going to involve some complicated dancing around the topic to pull it off without infuriating the girls, but he was confident he could make things work, and as he stepped out of the room confident Hifumi was having a great time, he pulled out his phone, wondering which girlfriend to call up next.


End file.
